Bridged disazo compounds

Abstract

Compounds of formula (I)with the meanings of D, R1, R2, X and Y as given in claim 1 can be used as paper dyes or direct dyes or for the preparation of ink-jet inks.

What is claimed is:  
     
       1. A compound of formula (I)                    
       wherein 
       D is a radical of a diazo component selected from the group having the formulae (a), (b), (c)                    
       A is OH or NH 2 ;  
       R 1  is independently H, C 1-4 alkyl;  
       R 2  is hydrogen, C 1-4 alkyl, C 1-4 alkoxy, halogen;  
       X is amino, mono- or di-C 1-3 alkylamino, mono- or di(hydroxy-C 2-4 alkyl)amino, monocarboxy-C 1-4 alkylamino, monosulpho-C 1-4 alkylamino, or morpholino,  
       Y is the radical of 4,4′-diamino-stilbene-2,2′-disulfonic acid;  
       m is 0, 1 or 2; and  
       n is 1 or 2;  
       or a salt thereof or a mixture of such compounds.  
     
     
       2. A compound according to  claim 1  having the formula (Ia)                    
       wherein R 1 , R 2 , X, Y and A have the meaning given in  claim 1 . 
     
     
       3. A compound according to  claim 1  having the formula (Ib)                    
       wherein R 1 , R 2 , m, n, X and Y have the meaning given in  claim 1 . 
     
     
       4. A compound according to  claim 1  having the formula (Ic)                    
       wherein R 1 , R 2 , X and Y have the meaning given in  claim 1 . 
     
     
       5. A process for the preparation of a compound of formula (I) according to  claim 1 , comprising reacting a compound of formula (IIa) having the following formula:                    
       with a diazotised compound of formula (IIb), having the following formula: 
       
         
           D—NH 2   (IIb)  
         
       
       so as to give a compound of formula (III), having the following formula:                    
       in which D and R 1  have the meaning given in  claim 1 , which compound is reacted with an appropriate diamino compound to give a compound of formula (I) in which X is halogen, after which such compound is further reacted with an appropriate amino compound to give a compound of formula (I) in which X is an amino group. 
     
     
       6. A process for the preparation of a compound of formula (I) according to  claim 1 , in which D is of formula (a) with A=OH and/or formula (c), comprising reacting the dyestuff of formula (IV)                    
       in which D and R 1  are as defined in  claim 1 , with cyanuric halogenide so as to give a compound of formula (III), having the following formula:                    
       in which D and R 1  are as defined in  claim 1 , which compound is reacted with an appropriate diamino compound to give a compound of formula (I) in which X is halogen, after which such compound is further reacted with an appropriate amino compound to give a compound of formula (I) in which X is an amino group. 
     
     
       7. A process according to  claim 5 , for the preparation of a compound of formula (Ia)                    
       in which A is OH in complex form, comprising the conversion of a metal-free compound of formula (Ia) into a 1:1 copper complex. 
     
     
       8. Process for dyeing or printing organic substrates containing hydroxy groups, thiol groups or nitrogen atoms, comprising the application of a compound of formula (I) according to  claim 1  to such substrates. 
     
     
       9. Process according to  claim 8  for dyeing or printing cellulosic textile materials or paper. 
     
     
       10. Organic substrates dyed or printed by the process of  claim 8 . 
     
     
       11. Process for the preparation of ink-jet inks, characterized in that a compound of formula (I) according to  claim 1  is used. 
     
     
       12. Ink-jet inks prepared by the process of  claim 11 . 
     
     
       13. A process for dyeing or printing organic substrate according to  claim 8  wherein said compound of formula (1) is selected from the group consisting of: paper dyes, direct dyes and ink jet inks.